One of the most storied hotels in all the Caribbean, El Convento was constructed in 1651 as a Carmelite nunnery, the first nunnery in the Americas. Though the original building was torn down and rebuilt in 1854, the historic ambiance of the place still harkens back to those early colonial times, thanks to such details as the Tuscan columns that guard the entrance, the exquisite latticed choir and the preserved historic details throughout. The inner courtyard, riotous with bougainvillea and leafy palms, holds one of the oldest trees in the city (it reached 300 several years back). Rooms are sumptuous steps back in time, with high ceilings striped with wooden beams, handmade tiles, pretty balconies, velvet settees and other elegant antiques. But don’t worry, if you’re more into fun in the sun than history, you’ll be well taken care of here, too. On the roof is a splash pool, Jacuzzi and sundeck (all have incredible vistas over the city); and guests have beach access at El Convento’s sister property. El Convento holds three restaurants, including a highly convivial tapas bar. There’s even a state–of–the-art fitness center. If any place ever embodied the phrase “best of both worlds” this would be it.